Asymmetric Synthesis of Highly Substituted β-Nitro Alcohols and Enantiomerically Enriched 4,4,5-Trisubstituted Oxazolidinones

Crich, David; Ranganathan, Krishnakumar; Rumthao, Sochanchingwung; Shirai, Michio

doi:10.1021/jo026707g

Cited by 25 publications

(9 citation statements)

References 30 publications

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“…As previously, the precursors of choice to the β-(phosphatoxy)alkyl radicals were the readily assembled, stable tertiary β-nitrophosphates. , This required the asymmetric synthesis of these substances, for which we have employed the Corey oxazaborolidine reduction of α,α-disubstituted-α-nitroketones developed in this laboratory . The absolute configurations of all nitro alcohols prepared were assigned following the standard Corey model, as rigorously established previously. , The synthesis of pyrrolidine and piperidine precursors 11 and 12 (Scheme ) was otherwise straightforward and proceeded from readily available materials.…”

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confidence: 99%

Enantioselective Cyclization of Alkene Radical Cations

2003

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[reaction: see text] Enantiomerically enriched beta-(diphenylphosphatoxy)nitroalkanes undergo radical ionic fragmentation, induced by tributyltin hydride and AIBN in benzene at reflux, to give alkene radical cations in contact radical ion pairs. These contact ion pairs are trapped intramolecularly by amines to give pyrrolidines and piperidines with significant enantioselectivity ( approximately 60% ee), indicative of cyclization competing effectively with equilibration within the ion pairs. Use of an intramolecular N-propargylamine as a nucleophile provides an enantiomerically enriched pyrrolizidine skeleton via a tandem polar/radical crossover sequence.

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confidence: 99%

Enantioselective Cyclization of Alkene Radical Cations

2003

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“…In addition to the examples shown above, several other syntheses of chiral oxazolidinones have also been reported [44][45][46][47][48][49][50][51][52][53]. These include the aminohydroxylation of allylic carbamates [44], catalytic intramolecular aminopalladation [45], polymer supported synthesis and combinatorial synthesis of oxazolidinone libraries [46][47][48], and the conversion of racemic terminal epoxides under kinetic resolution condition [49].…”

Section: Synthesis Of the 5-hydroxyl Methyl Oxazolidinone Core Structurementioning

confidence: 95%

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Wang¹

2008

AIAMC

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Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi antibiotic resistant Gram-positive bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido methyl oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamate 5-hydroxymethyloxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one are also important building blocks for synthesizing other biologically active compounds. Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of Linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships will be reviewed.

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“…Asymmetric nitroaldol reactions are often ineffective when secondary nitroalkanes are used as reagents because of a competitive retroaldol process. A stereocontrolled reduction of -nitro ketones 37 with borane in the presence of chiral oxazaborolidine 38 represents a valid option for the preparation of tertiary nitro alcohols 39 (Scheme 11) [29]. Reduction of the nitro group in usual conditions affords the corresponding amino alcohols 40 that without any further purification are directly converted into chiral oxazolidin-2-ones 41 [30].…”

Section: Amino Alcoholsmentioning

confidence: 99%

Nitroalkanes as Key Compounds for the Synthesis of Amino Derivatives

Ballini¹,

Gabrielli²,

Palmieri³

et al. 2011

COC

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The carbanion stabilizing effect of the nitro group makes nitroalkanes ideal reagents in carbon-carbon bond formation. Once introduced in a molecular framework, the nitro group is amenable to further transformations including reduction to primary amines. The aim of this review is to explore the utilization of nitroalkanes as effective substrates for the preparation of important target compounds featured by the amino group. These will include simple primary amines, diamines, amino acids, piperidines, pyrrolidines and heteroaromatic derivatives. A particular emphasis will be placed on the synthesis of enantioenriched amino derivatives mediated by organocatalysts or organometallic complexes.

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Asymmetric Synthesis of Highly Substituted β-Nitro Alcohols and Enantiomerically Enriched 4,4,5-Trisubstituted Oxazolidinones

Cited by 25 publications

References 30 publications

Enantioselective Cyclization of Alkene Radical Cations

Enantioselective Cyclization of Alkene Radical Cations

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

Nitroalkanes as Key Compounds for the Synthesis of Amino Derivatives

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